Project Title

Synthesis of alpha-Alkynyl- and Aziridinyl-phosphonates from alpha-Phosphonovinyl Triflates

Presenters

Academic department under which the project should be listed

CSM - Chemistry and Biochemistry

Faculty Sponsor Name

Christopher W. Alexander

IRB approval not required

Abstract (300 words maximum)

Alpha-phosphonovinyl triflates are a novel class of phosphonates that have been developed in our lab. We are exploring their chemical nature and have been successful in widening the synthetic scope of these molecules. For example, we have successfully used them as substrates in organopalladium catalyzed reactions to prepare alpha, beta-functionalized vinylphosphonates. Recently, we have developed a method to prepare alpha-alkynylphosphonates via a base promoted E2 reaction. Additionally, the triflates have been reacted with amines to afford alpha-aziridinylphosphonates via a Gabriel-Cromwell reaction. Interestingly, we have observed competing E2 and Gabriel-Cromwell reactions depending on the amine used. A summary of our method to synthesize alpha-alkynylphosphonates and alpha-aziridinylphosphonates from alpha-phosphonovinyl triflates will be presented.

Project Type

Poster

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Synthesis of alpha-Alkynyl- and Aziridinyl-phosphonates from alpha-Phosphonovinyl Triflates

Alpha-phosphonovinyl triflates are a novel class of phosphonates that have been developed in our lab. We are exploring their chemical nature and have been successful in widening the synthetic scope of these molecules. For example, we have successfully used them as substrates in organopalladium catalyzed reactions to prepare alpha, beta-functionalized vinylphosphonates. Recently, we have developed a method to prepare alpha-alkynylphosphonates via a base promoted E2 reaction. Additionally, the triflates have been reacted with amines to afford alpha-aziridinylphosphonates via a Gabriel-Cromwell reaction. Interestingly, we have observed competing E2 and Gabriel-Cromwell reactions depending on the amine used. A summary of our method to synthesize alpha-alkynylphosphonates and alpha-aziridinylphosphonates from alpha-phosphonovinyl triflates will be presented.